for yours to be correct Dubie needs to be basically a fucking narcissist, which we've seen no evidence of to date.
Why? I don't get it. I see this shit all day long, every day in my job. Maybe that's why I feel I see through this all so easily, while others are coming up with remote scenarios. From both sides, sometimes I rep the company, and sometimes the individual, but at all times you're always going for the max you can get based on the leverage you think you have.
Here, Dubie thought his worst case was taking the Shanny offer that was on the table, and that his best case was the Leafs advancing far or winning it all and then pushing his demands to the moon. So he waits. He strings Shanny along like the existing offer is all good, he gets the agent to be the buffer so that he's not directly communicating with Shanny about terms so as to get locked into any direct statement, and then lo and behold, the Leafs get to the second round!
Now Shanny approaches him again directly and he's still all non-committal about signing. But then the Leafs lose to Florida, in arguably a close series, but a loss nonetheless, so he only got a slight bit more in the form of talking points for the big ask, but you better believe, he's already been pricing out mansions with the $6M he has in his head that he was certain he'd get if the Leafs went far, and still relatively confident he can still get it they faltered. He certainly thinks public opinion is in his favor, that he has internal support, and that optics of losing the wonderkid that everyone around the league likes, will be too much for the Leafs to risk, especially with Matty and Willy extensions around the corner. But now he doesn't have a second or third round series win to bolster his bargaining position with MLSE. He still wants that extra money though, which is the equivalent of five bucks to the company, that he thinks he's earned after almost ten years of loyal service. So, he's going to go for it anyway.
But he needs a new approach. So, he has to make it look like this high pressure, high visibility job is really taking a toll on the family. Making this great guy have to actually consider maybe giving up his dream job to spare his fam from the rigors of the day to day life of being tied to the Leafs' fortunes. Woe is them. He's already made some noise about this to Shanny, but he needs to up the ante, get the media to put the fear of god into Shanny and the Leafs that he might not return. So he holds the presser that Shanny told him not to hold yet, and then says he doesn't know what he's doing next season. Naturally, he thinks he's covered himself by saying he WON'T go with another team, thereby demonstrating his devotion to the franchise, and keeping that worst case scenario of just signing the existing offer open to fall back on. Enter new, last minute financial demands, which make clear for anyone watching, that family was never a thing, money was. And if he threw something in there about autonomy, then even worse.
Shanny sees right through these antics, loses all respect for the guy, and starts considering a new direction likely from both the now more objective viewpoint on the team's mostly stagnant progress, and personal distaste for his kid protege trying to play him and maybe even plant the seeds for a power grab of some sort. Shanny pulls the rug out from under him, leaving him in shock and fucking embarrassed to have made stupid statements like maybe taking a year off, and Dubie can't hide his anger, as he immediately unfollows the Leafs and Shanny on social media and starts leaking stuff about Board interference being a factor in his hesitation to re-up.
Pittsburgh has its GM job vacant and calls him up for an interview. The Dubas Family somehow gathers itself together to send its representative to meet with the Pens, and boom, back to work next week-ish.
I can't prove it, but this is 99.9% what happened to this point based on all the available information.